5,6-Dimethoxy-1-(4-tolylsulfonyl)benzo[c]isoxazol-3(1H)-one

The title compound, C₁₆H₁₅N₁O₆S, was synthesized by reacting 5,6-dimethoxy­benzo[c]isoxazol-3(1H)-one with 4-methyl­benzene­sulfonyl chloride in dichloromethane chloride, using triethyl­amine as the base and 4-(dimethyl­amino)pyridine as catalyst.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.126
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

5,6-Dimethoxy-1-(toluene-4-sulfonyl)benzo[c]isoxazol-3(1H)-one

Crystal data

C16H15NO6S	Z = 2
Mr = 349.35	F(000) = 364
Triclinic, P1	Dx = 1.413 Mg m^−3
Hall symbol: -P 1	Melting point = 543–544 K
a = 8.595 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.868 (2) Å	Cell parameters from 850 reflections
c = 11.628 (3) Å	θ = 2.9–25.8°
α = 77.197 (4)°	µ = 0.23 mm^−1
β = 79.270 (4)°	T = 293 K
γ = 73.478 (4)°	Block, colorless
V = 821.4 (3) Å^3	0.36 × 0.34 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2903 independent reflections
Radiation source: fine-focus sealed tube	2000 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan SADABS (Bruker, 1997)	h = −10→10
Tmin = 0.889, Tmax = 1.000	k = −5→10
4330 measured reflections	l = −13→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0596P)^2 + 0.1843P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.126	(Δ/σ)max = 0.004
S = 1.05	Δρmax = 0.23 e Å^−3
2903 reflections	Δρmin = −0.27 e Å^−3
220 parameters

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.16942 (9)	0.69500 (8)	0.13648 (6)	0.0636 (3)
O1	0.0607 (3)	0.7639 (3)	0.05000 (18)	0.0853 (6)
O2	0.2746 (3)	0.5394 (2)	0.13681 (17)	0.0754 (6)
O3	0.4018 (2)	0.3466 (2)	0.56627 (14)	0.0614 (5)
O4	0.2505 (2)	0.5311 (2)	0.71094 (15)	0.0683 (5)
O5	−0.1823 (2)	0.9711 (3)	0.4186 (2)	0.0896 (7)
O6	−0.0743 (2)	0.8204 (2)	0.27825 (18)	0.0705 (5)
N1	0.0452 (3)	0.6713 (3)	0.2691 (2)	0.0610 (6)
C1	−0.0832 (3)	0.8554 (3)	0.3906 (3)	0.0648 (7)
C2	0.0384 (3)	0.7300 (3)	0.4520 (2)	0.0531 (6)
C3	0.0759 (3)	0.7047 (3)	0.5677 (2)	0.0562 (6)
H3	0.0197	0.7747	0.6192	0.067*
C4	0.1980 (3)	0.5733 (3)	0.6029 (2)	0.0508 (6)
C5	0.1574 (4)	0.6149 (4)	0.8025 (3)	0.0882 (10)
H5A	0.1588	0.7254	0.7804	0.132*
H5B	0.2040	0.5694	0.8752	0.132*
H5C	0.0465	0.6063	0.8136	0.132*
C6	0.2829 (3)	0.4681 (3)	0.5222 (2)	0.0482 (6)
C7	0.4924 (3)	0.2320 (3)	0.4932 (2)	0.0649 (7)
H7A	0.4193	0.1807	0.4729	0.097*
H7B	0.5740	0.1533	0.5358	0.097*
H7C	0.5447	0.2852	0.4218	0.097*
C8	0.2414 (3)	0.4918 (3)	0.4092 (2)	0.0484 (6)
H8	0.2943	0.4212	0.3574	0.058*
C9	0.1172 (3)	0.6257 (3)	0.3766 (2)	0.0491 (6)
C10	0.2780 (3)	0.8294 (3)	0.1465 (2)	0.0542 (6)
C11	0.2114 (3)	0.9920 (3)	0.1161 (2)	0.0655 (7)
H11	0.1086	1.0306	0.0907	0.079*
C12	0.3001 (4)	1.0960 (3)	0.1240 (3)	0.0711 (8)
H12	0.2552	1.2055	0.1044	0.085*
C13	0.4533 (3)	1.0419 (3)	0.1601 (2)	0.0626 (7)
C14	0.5166 (3)	0.8787 (4)	0.1892 (2)	0.0664 (8)
H14	0.6199	0.8402	0.2137	0.080*
C15	0.4316 (3)	0.7717 (3)	0.1831 (2)	0.0624 (7)
H15	0.4765	0.6623	0.2032	0.075*
C16	0.5504 (4)	1.1549 (4)	0.1676 (3)	0.0880 (10)
H16A	0.4942	1.2623	0.1364	0.132*
H16B	0.6565	1.1273	0.1220	0.132*
H16C	0.5629	1.1475	0.2492	0.132*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0718 (5)	0.0641 (5)	0.0536 (4)	−0.0063 (4)	−0.0273 (3)	−0.0062 (3)
O1	0.0988 (15)	0.0907 (15)	0.0709 (13)	−0.0159 (12)	−0.0499 (12)	−0.0020 (11)
O2	0.0951 (15)	0.0609 (12)	0.0642 (12)	0.0004 (11)	−0.0222 (11)	−0.0155 (9)
O3	0.0666 (11)	0.0558 (10)	0.0488 (10)	0.0079 (9)	−0.0132 (8)	−0.0084 (8)
O4	0.0726 (12)	0.0799 (13)	0.0523 (10)	−0.0085 (10)	−0.0083 (9)	−0.0254 (9)
O5	0.0584 (12)	0.0679 (13)	0.1277 (19)	0.0108 (11)	−0.0120 (12)	−0.0221 (13)
O6	0.0489 (11)	0.0695 (12)	0.0856 (14)	−0.0008 (9)	−0.0222 (10)	−0.0056 (10)
N1	0.0530 (13)	0.0578 (13)	0.0697 (14)	−0.0058 (11)	−0.0216 (11)	−0.0061 (11)
C1	0.0417 (14)	0.0548 (16)	0.094 (2)	−0.0071 (13)	−0.0084 (14)	−0.0114 (15)
C2	0.0418 (13)	0.0467 (14)	0.0702 (17)	−0.0122 (11)	−0.0064 (12)	−0.0090 (12)
C3	0.0491 (14)	0.0514 (15)	0.0708 (17)	−0.0133 (12)	0.0021 (13)	−0.0240 (13)
C4	0.0497 (14)	0.0532 (14)	0.0521 (14)	−0.0143 (12)	−0.0058 (11)	−0.0140 (12)
C5	0.097 (2)	0.107 (3)	0.0686 (19)	−0.019 (2)	−0.0035 (17)	−0.0463 (19)
C6	0.0483 (13)	0.0433 (13)	0.0509 (14)	−0.0103 (11)	−0.0045 (11)	−0.0079 (11)
C7	0.0624 (16)	0.0570 (16)	0.0630 (16)	0.0042 (13)	−0.0040 (13)	−0.0141 (13)
C8	0.0513 (14)	0.0419 (13)	0.0503 (13)	−0.0090 (11)	−0.0073 (11)	−0.0077 (10)
C9	0.0463 (13)	0.0470 (13)	0.0557 (14)	−0.0149 (11)	−0.0107 (11)	−0.0055 (11)
C10	0.0545 (15)	0.0589 (15)	0.0407 (12)	−0.0021 (12)	−0.0122 (11)	−0.0023 (11)
C11	0.0582 (16)	0.0646 (18)	0.0632 (17)	0.0017 (14)	−0.0176 (13)	−0.0040 (13)
C12	0.0744 (19)	0.0559 (16)	0.0719 (19)	−0.0032 (15)	−0.0083 (15)	−0.0073 (14)
C13	0.0667 (18)	0.0736 (19)	0.0425 (14)	−0.0144 (15)	−0.0007 (12)	−0.0100 (13)
C14	0.0552 (16)	0.084 (2)	0.0535 (15)	−0.0136 (15)	−0.0158 (12)	0.0026 (14)
C15	0.0572 (16)	0.0648 (17)	0.0523 (15)	−0.0030 (14)	−0.0145 (12)	0.0055 (12)
C16	0.100 (2)	0.100 (2)	0.075 (2)	−0.039 (2)	−0.0035 (18)	−0.0241 (18)

Geometric parameters (Å, º)

S1—O2	1.4176 (19)	C6—C8	1.381 (3)
S1—O1	1.4181 (18)	C7—H7A	0.9600
S1—N1	1.713 (2)	C7—H7B	0.9600
S1—C10	1.743 (3)	C7—H7C	0.9600
O3—C6	1.338 (3)	C8—C9	1.387 (3)
O3—C7	1.431 (3)	C8—H8	0.9300
O4—C4	1.352 (3)	C10—C11	1.383 (4)
O4—C5	1.421 (3)	C10—C15	1.384 (3)
O5—C1	1.197 (3)	C11—C12	1.379 (4)
O6—C1	1.392 (3)	C11—H11	0.9300
O6—N1	1.436 (3)	C12—C13	1.378 (4)
N1—C9	1.426 (3)	C12—H12	0.9300
C1—C2	1.451 (4)	C13—C14	1.382 (4)
C2—C9	1.365 (3)	C13—C16	1.500 (4)
C2—C3	1.396 (4)	C14—C15	1.372 (4)
C3—C4	1.371 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C6	1.424 (3)	C16—H16A	0.9600
C5—H5A	0.9600	C16—H16B	0.9600
C5—H5B	0.9600	C16—H16C	0.9600
C5—H5C	0.9600
O2—S1—O1	120.79 (12)	H7A—C7—H7B	109.5
O2—S1—N1	102.30 (12)	O3—C7—H7C	109.5
O1—S1—N1	104.86 (12)	H7A—C7—H7C	109.5
O2—S1—C10	110.72 (12)	H7B—C7—H7C	109.5
O1—S1—C10	110.38 (12)	C6—C8—C9	116.9 (2)
N1—S1—C10	106.32 (11)	C6—C8—H8	121.6
C6—O3—C7	118.75 (19)	C9—C8—H8	121.6
C4—O4—C5	117.9 (2)	C2—C9—C8	122.1 (2)
C1—O6—N1	108.90 (18)	C2—C9—N1	110.0 (2)
C9—N1—O6	105.76 (19)	C8—C9—N1	127.8 (2)
C9—N1—S1	118.65 (16)	C11—C10—C15	120.6 (3)
O6—N1—S1	108.35 (15)	C11—C10—S1	119.9 (2)
O5—C1—O6	119.5 (3)	C15—C10—S1	119.4 (2)
O5—C1—C2	133.4 (3)	C12—C11—C10	118.9 (3)
O6—C1—C2	107.2 (2)	C12—C11—H11	120.6
C9—C2—C3	121.5 (2)	C10—C11—H11	120.6
C9—C2—C1	107.9 (2)	C13—C12—C11	121.7 (3)
C3—C2—C1	130.5 (2)	C13—C12—H12	119.1
C4—C3—C2	117.9 (2)	C11—C12—H12	119.1
C4—C3—H3	121.0	C12—C13—C14	117.9 (3)
C2—C3—H3	121.0	C12—C13—C16	121.8 (3)
O4—C4—C3	125.8 (2)	C14—C13—C16	120.3 (3)
O4—C4—C6	114.1 (2)	C15—C14—C13	122.0 (3)
C3—C4—C6	120.1 (2)	C15—C14—H14	119.0
O4—C5—H5A	109.5	C13—C14—H14	119.0
O4—C5—H5B	109.5	C14—C15—C10	118.8 (3)
H5A—C5—H5B	109.5	C14—C15—H15	120.6
O4—C5—H5C	109.5	C10—C15—H15	120.6
H5A—C5—H5C	109.5	C13—C16—H16A	109.5
H5B—C5—H5C	109.5	C13—C16—H16B	109.5
O3—C6—C8	124.2 (2)	H16A—C16—H16B	109.5
O3—C6—C4	114.3 (2)	C13—C16—H16C	109.5
C8—C6—C4	121.4 (2)	H16A—C16—H16C	109.5
O3—C7—H7A	109.5	H16B—C16—H16C	109.5
O3—C7—H7B	109.5
C1—O6—N1—C9	−4.9 (2)	C4—C6—C8—C9	2.2 (3)
C1—O6—N1—S1	−133.06 (18)	C3—C2—C9—C8	−1.8 (4)
O2—S1—N1—C9	62.1 (2)	C1—C2—C9—C8	180.0 (2)
O1—S1—N1—C9	−170.99 (19)	C3—C2—C9—N1	174.5 (2)
C10—S1—N1—C9	−54.0 (2)	C1—C2—C9—N1	−3.8 (3)
O2—S1—N1—O6	−177.38 (14)	C6—C8—C9—C2	−0.2 (3)
O1—S1—N1—O6	−50.51 (17)	C6—C8—C9—N1	−175.7 (2)
C10—S1—N1—O6	66.44 (16)	O6—N1—C9—C2	5.3 (3)
N1—O6—C1—O5	−176.1 (2)	S1—N1—C9—C2	127.13 (19)
N1—O6—C1—C2	2.7 (3)	O6—N1—C9—C8	−178.7 (2)
O5—C1—C2—C9	179.2 (3)	S1—N1—C9—C8	−56.9 (3)
O6—C1—C2—C9	0.7 (3)	O2—S1—C10—C11	162.7 (2)
O5—C1—C2—C3	1.2 (5)	O1—S1—C10—C11	26.3 (3)
O6—C1—C2—C3	−177.4 (2)	N1—S1—C10—C11	−86.9 (2)
C9—C2—C3—C4	1.7 (4)	O2—S1—C10—C15	−16.2 (2)
C1—C2—C3—C4	179.5 (2)	O1—S1—C10—C15	−152.7 (2)
C5—O4—C4—C3	9.8 (4)	N1—S1—C10—C15	94.1 (2)
C5—O4—C4—C6	−170.8 (2)	C15—C10—C11—C12	−0.6 (4)
C2—C3—C4—O4	179.7 (2)	S1—C10—C11—C12	−179.6 (2)
C2—C3—C4—C6	0.3 (3)	C10—C11—C12—C13	0.7 (4)
C7—O3—C6—C8	−0.4 (3)	C11—C12—C13—C14	−0.4 (4)
C7—O3—C6—C4	178.7 (2)	C11—C12—C13—C16	179.4 (3)
O4—C4—C6—O3	−1.0 (3)	C12—C13—C14—C15	0.0 (4)
C3—C4—C6—O3	178.5 (2)	C16—C13—C14—C15	−179.8 (2)
O4—C4—C6—C8	178.3 (2)	C13—C14—C15—C10	0.1 (4)
C3—C4—C6—C8	−2.3 (4)	C11—C10—C15—C14	0.3 (4)
O3—C6—C8—C9	−178.7 (2)	S1—C10—C15—C14	179.23 (19)